What do you do when you have 2 dates in one week?

I really have to put myself out there, being a male and 39, so I have to send out messages to anyone I see with potential. Rarely do I get anything back and only go on a few dates a year, but now I have 2 dates almost one after the other, 1 or 2 days apart. Is it wrong to do that? I see a lot of potential in both, though both are 20 minutes and in the city, while I'm in the suburbs. I might even want to give both 2nd dates to make sure.. but it just seems odd doing this. If the first one goes well, what do I tell the other? I have a 2nd date with someone else? It'll be hard enough driving and parking in the city... in Chicago it's like $20+ to park somewhere. Logistically I'm not sure what to do here. Both are scheduled on the weekdays.

On the other hand, my 6 year long (now ex) and I are still hanging out like nothing changed a year ago, and we see each other every weekend and Wednesday until we find someone else right for us, that's our arrangement. She's also my only hangout friend, so it just helps me on that level too, and part of why it was hard for me to completely break it completely with her. So, when we have a date we actually don't let the other know because it would hurt, but the promise is to not have sex, give someone 2 dates and if they seem right, then that's it.



Submitted September 04, 2021 at 11:57PM

I really have to put myself out there, being a male and 39, so I have to send out messages to anyone I see with potential. Rarely do I get anything back and only go on a few dates a year, but now I have 2 dates almost one after the other, 1 or 2 days apart. Is it wrong to do that? I see a lot of potential in both, though both are 20 minutes and in the city, while I'm in the suburbs. I might even want to give both 2nd dates to make sure.. but it just seems odd doing this. If the first one goes well, what do I tell the other? I have a 2nd date with someone else? It'll be hard enough driving and parking in the city... in Chicago it's like $20+ to park somewhere. Logistically I'm not sure what to do here. Both are scheduled on the weekdays.On the other hand, my 6 year long (now ex) and I are still hanging out like nothing changed a year ago, and we see each other every weekend and Wednesday until we find someone else right for us, that's our arrangement. She's also my only hangout friend, so it just helps me on that level too, and part of why it was hard for me to completely break it completely with her. So, when we have a date we actually don't let the other know because it would hurt, but the promise is to not have sex, give someone 2 dates and if they seem right, then that's it.
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